Cross Country Considerations II: Vacations

Mike Peluso
11 min readJun 13, 2022

I recently went on a very unique vacation…

I recently went on a very unique vacation. I went with some friends, the Bowers. More specifically, I went with my friend Don and his daughter Ginny, although we just refer to her by her nickname Gin. Initially it was just supposed to be a fishing trip with me and Don, but as time went on, it morphed into a quasi family trip. Gin often vacations with her dad, and since Gin is a single mom she has to bring her kid pretty much everywhere she goes as his dad is completely out of the picture. Since she brought her kid, I brought mine as they are fast friends as it’s always better for kids to have a friend while on vacation. Since there were three of them, two of which had birthdays that week, and they picked up the room, we mostly vacationed by their schedule and followed their family traditions. That was the first important point, I was exposed to a type of vacation that was out of my comfort zone. The second point, one I already alluded to, was that it was just me and my kid, something I hadn’t done before. These two experiences in conjunction with something else going on in my life brought about some serious reflection on vacationing. Ultimately, I had what I thought of as a bit of a vacation oriented existential crisis.

When I was single, before children, vacations really meant going to see family. This made sense as I wasn’t very self confident about exploring the world on my own and the ties to my youthful network of friends were still strong. Things didn’t change that much after I got into a relationship, and ultimately got married. My vacations mostly stayed the same. We just had two families to visit instead of one. Also, even in the first years of marriage, I was in the early part of my career, so spending money on big vacations seemed exorbitant. As a bit of time went on, we would start to go on trips just by ourselves, usually to see or experience something new, but that was mostly limited to long weekends and destinations you could reach by car, with the only exception being cruises. We went on a bunch of those because we owned Piedmont Cruises, a small home based travel agency, as our side hustle. The cruises were especially valuable in helping me form theories on what you should and, more importantly, should not do on vacations. Between the family trips, the couples…

Mike Peluso

Mike Peluso writes is about the collision between the professional world and life. Read more at or listen to the Peluso Presents Podcast